KR960010648A - Oxazoloquinolinone derivatives and their preparation and therapeutic uses - Google Patents

Oxazoloquinolinone derivatives and their preparation and therapeutic uses Download PDF

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KR960010648A
KR960010648A KR1019950028714A KR19950028714A KR960010648A KR 960010648 A KR960010648 A KR 960010648A KR 1019950028714 A KR1019950028714 A KR 1019950028714A KR 19950028714 A KR19950028714 A KR 19950028714A KR 960010648 A KR960010648 A KR 960010648A
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제강 사미르
쟈끄 캐니그 쟝
뷔에슈 프레데릭
삐르니에 삘리쁘
자르 리디아
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에. 뚜레 레메뜨르
신떼라보 소시에떼 아노님
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Abstract

3,3a,4,5-tetrahydro-1H-oxazolo (3,4-a) quinolin-1-one derivs. of formula (I) and their isomers are new. n = 0 or 1; R1 = H, Me, Et, vinyl, phenyl, CH2OH or CH2OMe; and either R2 = Me, CF3 or CN, R3 = H, OH or benzyloxy, and R4, R5 = H; or R2+R4 = (OCH2)4, R3 = OH and R5 = H; or R2+R5 = O(CH2)3 and R3 = R4 = H; or R2+R5 = (CH2)4, R3 = OH and R4 = H.

Description

옥사졸로퀴놀린온 유도체와 그것의 제법 및 체료적 이용Oxazoloquinolinone derivatives and their preparation and physical use

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (12)

거울상 이성질체 및 부분입체 이성질체를 포함한 이성질체의 형태 및 라세미 혼합물을 포함한 이들 각종형태의 혼합물의 형태의 다음 일반식(Ⅰ)의 3,3a,4,5-테트라히드로-1H-옥사졸로[3,4-a]퀴놀린-1-온 유도체3,3a, 4,5-tetrahydro-1H-oxazolo [3, in the form of isomers, including enantiomers and diastereomers, and mixtures of these various forms, including racemic mixtures 4-a] quinolin-1-one derivative [식에서, n은 0 또는 1이고, R1은 수소원자, 에텐일기, 메틸기, 에틸기, 페닐기, 히드록시메킬기 또는 메톡시메킬기를 나타내고, R2는 메틸기, 트리플루오로메틸기 또는 시아노기이고, R3은 수소원자, 히드록실기 또는 벤질옥식이고, R4및 R5는 수소원자이거나, 또는 R2및 R4는 함께-(CH2)4-기를 형성하고, R3은 히드록실기이고, R5는 수소원자이거나. 또는 R2및 R5는 함께 -O-(CH2)3-기를 형성하고, R3및 R4는 수소원자이거나, 또는 R2및 R5는 함께 -(CH2)4-기를 형성하고, R3은 히드록실기이고, R4는 수소원자이다.][Wherein n is 0 or 1, R 1 represents a hydrogen atom, an ethenyl group, a methyl group, an ethyl group, a phenyl group, a hydroxymethyl group or a methoxymethyl group, R 2 is a methyl group, a trifluoromethyl group or a cyano group, R 3 is a hydrogen atom, hydroxyl group or benzyloxy, R 4 and R 5 are hydrogen atoms, or R 2 and R 4 together form a-(CH 2 ) 4 -group, R 3 is a hydroxyl group , R 5 is a hydrogen atom. Or R 2 and R 5 together form a —O— (CH 2 ) 3 — group, R 3 and R 4 together are a hydrogen atom, or R 2 and R 5 together form a — (CH 2 ) 4 — group, R 3 is a hydroxyl group and R 4 is a hydrogen atom.] 3-메톡시메틸-7-(4,4,4-트리플루오로-3-히드록시부톡시)-3, 3a,4,5-테트라히드로-1H-옥사졸로[3,4-a]퀴놀린-1-온, 및 순수하거나 또는 혼합물의 형태인 그 거울상 이성질체 및 부분입체 이성질체.3-methoxymethyl-7- (4,4,4-trifluoro-3-hydroxybutoxy) -3,3a, 4,5-tetrahydro-1H-oxazolo [3,4-a] quinoline -1-ones and their enantiomers and diastereomers in the form of pure or mixtures. 3-메톡시메틸-7-(4,4,4-트리플루오로부톡시-3,a,4,5-테트라히드로-1H-옥사졸로[3,4-a]퀴놀린-1-온, 및 순수하거나 또는 혼합물의 형태인 그 거울상 이성질체 및 부분입체 이성질체.3-methoxymethyl-7- (4,4,4-trifluorobutoxy-3, a, 4,5-tetrahydro-1H-oxazolo [3,4-a] quinolin-1-one, and Enantiomers and diastereomers thereof, either pure or in the form of a mixture. 7-(4,4,4-트리플루오로부톡시-3,3a,4,5-테트라히드로-1H-옥사졸로[3,4-a]퀴놀린-1-온, 및 순수하거나 또는 혼합물의 형태인 그 거울상 이성질체 및 부분입체 이성질체.7- (4,4,4-trifluorobutoxy-3,3a, 4,5-tetrahydro-1H-oxazolo [3,4-a] quinolin-1-one, and either pure or in the form of a mixture Its enantiomers and diastereomers. 7-(3-히드록시-4,4,4-트리플루오로부톡시-3,3a,4,5-테트라히드로-1H-옥사졸로[3,4-a]퀴놀린-1-온, 및 순수하거나 또는 혼합물의 형태인 그 거울상 이성질체 및 부분입체 이성질체.7- (3-hydroxy-4,4,4-trifluorobutoxy-3,3a, 4,5-tetrahydro-1H-oxazolo [3,4-a] quinolin-1-one, and pure water Enantiomers and diastereomers thereof in the form of a mixture or a mixture thereof. 3-메톡시메틸-7-[(2(1-히드록시시클로펜틸)에톡시]-3,3a,4,5-테트라히드로-1H-옥사졸로[3,4-a]퀴놀린-1-온, 및 순수하거나 또는 혼합물의 형태인 그 거울상 이성질체 및 부분입체 이성질체.3-methoxymethyl-7-[(2 (1-hydroxycyclopentyl) ethoxy] -3,3a, 4,5-tetrahydro-1H-oxazolo [3,4-a] quinolin-1-one And enantiomers and diastereomers thereof, either pure or in the form of a mixture. 식(Ⅱ)Formula (Ⅱ) (식에서, R1은 수소원자, 에텐일기, 페닐기. 히드록시메틸기 또는 메톡시메틸기를 나타낸다.)의 화합물을 식(Ⅲ)Wherein R 1 represents a hydrogen atom, an ethenyl group, a phenyl group, a hydroxymethyl group or a methoxymethyl group. (식에서, R2,R3,R4,R5및 n은 1항에서와 같이 정의되고, X는 할로겐원자 또는 메실옥시 또는 토실옥시와 같은 불안정 기이다.)의 화합물로 처리하여 R1이 상기와 같이 정의되고 식(Ⅰ)의화합물을 얻은 다음 R1이 에텐일기인 식(Ⅰ)의 화합물을 환원시켜 R1이 에틸기인 식(Ⅰ)의 화합물을 얻는 것을 특징으로 하는 식(Ⅰ)의화합물의 제조방법.By treatment of a compound of (wherein, R 2, R 3, R 4, R 5 and n are defined as in 1, wherein, X is a stable group such as a halogen atom or a mesyl oxy or tosyloxy.) The R 1 Formula (I), wherein the compound of formula (I) is defined as above and the compound of formula (I) wherein R 1 is an ethenyl group is reduced to obtain a compound of formula (I) wherein R 1 is an ethyl group. Process for the preparation of the compound. 제7항에 있어서, 식(Ⅱ)의 화합물의 대응 이성질체를 출발물질오서 사용하는 것을 특징으로 하는 식(Ⅰ)의 화합물의 거울상 이성질체 및 부분입체 이성질체의 제조방법.8. The method for preparing enantiomers and diastereomers of the compound of formula (I) according to claim 7, wherein the corresponding isomer of the compound of formula (II) is used as a starting material. 제7항에 있어서, 식(Ⅱ)의 거울상 이성질체 또는 부분입체 이성질체는 식(Ⅳ)8. The enantiomer or diastereomer of formula (II) according to claim 7, wherein the enantiomer or diastereomer of formula (II) 또는 식(Ⅴ)Or formula (Ⅴ) (식에서 R1은 에텐일기. 메틸기 또는 페닐기를 나타낸다.)의 화합물의거울상 이성질체 또는 부분 입체 이성질체로 부터 제조하고, 그것들은 에틸 2-메톡시카르보닐-6-메톡시-1,2,3,4-테트라히드로퀴놀린-1-카르복실레이트를 효소 가수분해하고, 에틸 2-메톡시카르보닐-6-메톡시-1,2,3,4-테트라히드로퀴놀린-1-카르복실레이트의 s(-) 거울상 이성질체와 에틸 2-카르복시-6-메톡시-1,2,3,4-테트라히드로퀴놀린-1-카르복실레이트의 R(+) 거울상 이성질체를 염화 티오닐 및 메탄올로 처리하여 대응 2-메톡시카르보닐 유도체를 유도하고, 2-메톡시카보닐 유도체의 s(-)및 R(+) 거울상 이성질체를 수소화붕소리튬과 반응시켜 식(Ⅳ)의 화합물의 S(+) 및 R(-) 거울상 이성질체를 각각 얻거나, 또는 수소화디이소부틸알루미늄과 반응시켜, 식 R1MgX(식에서, R1은 상기와 같이 정의되고 x는 할로겐원자이다.)의 유기마그네슘 화합물로 다음에 메톡시하나트륨으로 처리하고 최종적으로 크로마토그래피로 분리시 식(Ⅴ)의 부분입체 이성질체를 유도하는 대응 2-포르밀 유도체의 S(-) 및 R(+) 거울상 이성질체를 각각 얻음으로써 얻어지는 것을 특징으로 하는 제조방법.Wherein R 1 represents an ethenyl group. Methyl group or phenyl group. Prepared from enantiomers or diastereomers, they are ethyl 2-methoxycarbonyl-6-methoxy-1,2,3, Enzymatic hydrolysis of 4-tetrahydroquinoline-1-carboxylate was carried out to obtain s (of ethyl 2-methoxycarbonyl-6-methoxy-1,2,3,4-tetrahydroquinoline-1-carboxylate) -) Enantiomers and R (+) enantiomers of ethyl 2-carboxy-6-methoxy-1,2,3,4-tetrahydroquinoline-1-carboxylate were treated with thionyl chloride and methanol to counteract 2 Inducing methoxycarbonyl derivatives and reacting the s (-) and R (+) enantiomers of the 2-methoxycarbonyl derivatives with lithium borohydride to give the S (+) and R ( -) to obtain the enantiomer, respectively, or diisobutylaluminum hydride and reacting the formula R 1 MgX (formula, R 1 is as defined above And x is a halogen atom. S (-) of the corresponding 2-formyl derivative which induces diastereoisomers of formula (V) upon treatment with sodium methoxy halo and finally chromatographic separation. ) And R (+) enantiomers, respectively. 제8하에 있어서, 효소 가수분해는 돼지 간 에스테라제 또는 말. 돼지, 소, 토끼 또는 양 간 아세톤 분말과 같은 효소 추출물에 의해 수행되는 것ㅇ르 특징으로 하는 에틸 2-메톡시카르보닐-6-메톡시-1,2,3,4,-테트라히드로퀴놀린-1-카르복실레이트의 거울상 이성질체의 제조방법.The method of claim 8, wherein the enzymatic hydrolysis is pig liver esterase or horse. Ethyl 2-methoxycarbonyl-6-methoxy-1,2,3,4, -tetrahydroquinoline-characterized by enzyme extracts such as pig, cow, rabbit or sheep liver acetone powder Method for preparing enantiomers of 1-carboxylate. 제1하에 따른 식(Ⅰ)의 화합물로 구성되는 것을 특징으로 하는 약제.A pharmaceutical comprising the compound of formula (I) according to claim 1. 제1항에 따른 식(Ⅰ)의 화합물을 어떤 적당한 부형제와 조합하여 함유하는 것을 특징으로 하는 의약 조성물.A pharmaceutical composition comprising the compound of formula (I) according to claim 1 in combination with any suitable excipient. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019950028714A 1994-09-05 1995-09-04 Oxazoloquinolinone derivatives, their preparation and their therapeutic application KR100392523B1 (en)

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FR9410600A FR2724171B1 (en) 1994-09-05 1994-09-05 DERIVATIVES OF 3.3A, 4,5-TETRAHYDRO-1H-OXAZOLO (3,4-A) QUINOLEIN-1-ONE, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION
FR94-10600 1994-09-05

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